#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/12/7151235.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151235
loop_
_publ_author_name
'Hussaini, Syed Raziullah'
'Moloney, Mark G.'
_publ_section_title
;
 2,5-Disubstituted pyrrolidines: synthesis by enamine reduction and
 subsequent regioselective and diastereoselective alkylations.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2600
_journal_page_last               2615
_journal_paper_doi               10.1039/b604183c
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C33 H37 N1 O6 '
_chemical_formula_sum            'C33 H37 N O6'
_chemical_formula_weight         543.66
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.6345(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3002(2)
_cell_length_b                   33.6715(4)
_cell_length_c                   10.5310(2)
_cell_measurement_reflns_used    17333
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     2943.03(10)
_computing_cell_refinement
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Nonius KappaCCD
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17333
_diffrn_reflns_theta_full        27.489
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         5.207
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       ' plate '
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.14
_exptl_crystal_thermal_history
;
The material was crystallised at ambient temperature. A suitable crystal
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis.
;
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0425
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         4668
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.002088
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
1.67 0.134 1.28
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0561
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0531
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              43
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                4668
_reflns_number_total             6438
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            b604183c.txt
_cod_data_source_block           ac397
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        ' C33 H37 N1 O6 '
_cod_database_code               7151235
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
N1 N 0.1729(4) 0.68445(9) 0.1990(3) 0.0255 1.0000 Uani
C1 C 0.3405(4) 0.67161(11) 0.2259(4) 0.0269 1.0000 Uani
C2 C 0.3359(5) 0.65873(13) 0.3650(4) 0.0340 1.0000 Uani
C3 C 0.1589(5) 0.64863(12) 0.3890(4) 0.0317 1.0000 Uani
C4 C 0.0642(4) 0.67806(11) 0.3067(3) 0.0271 1.0000 Uani
C5 C 0.1377(5) 0.70475(11) 0.0909(4) 0.0305 1.0000 Uani
O1 O 0.2442(4) 0.71442(8) 0.0165(3) 0.0369 1.0000 Uani
C6 C -0.0380(5) 0.71280(12) 0.0611(4) 0.0381 1.0000 Uani
C7 C 0.3909(4) 0.63917(10) 0.1297(3) 0.0242 1.0000 Uani
C8 C 0.5715(4) 0.63321(11) 0.1330(3) 0.0262 1.0000 Uani
O2 O 0.6636(3) 0.65019(9) 0.2019(3) 0.0355 1.0000 Uani
O3 O 0.6145(3) 0.60705(8) 0.0426(3) 0.0312 1.0000 Uani
C9 C 0.7871(5) 0.59868(14) 0.0363(5) 0.0428 1.0000 Uani
C10 C 0.8107(6) 0.56814(16) -0.0649(5) 0.0505 1.0000 Uani
C11 C 0.2978(4) 0.60053(11) 0.1466(3) 0.0249 1.0000 Uani
O4 O 0.1687(4) 0.59413(9) 0.0993(3) 0.0422 1.0000 Uani
O5 O 0.3761(3) 0.57559(8) 0.2230(3) 0.0310 1.0000 Uani
C12 C 0.2952(5) 0.53785(12) 0.2499(4) 0.0356 1.0000 Uani
C13 C 0.4186(6) 0.51031(12) 0.3052(4) 0.0440 1.0000 Uani
C14 C 0.0423(5) 0.71775(11) 0.3761(4) 0.0286 1.0000 Uani
O6 O -0.0702(3) 0.71072(7) 0.4739(2) 0.0289 1.0000 Uani
C15 C -0.1226(4) 0.74539(10) 0.5440(3) 0.0251 1.0000 Uani
C16 C -0.2237(4) 0.72798(11) 0.6526(4) 0.0293 1.0000 Uani
C17 C -0.2668(5) 0.68847(13) 0.6558(5) 0.0409 1.0000 Uani
C18 C -0.3591(6) 0.67416(16) 0.7552(6) 0.0576 1.0000 Uani
C19 C -0.4105(5) 0.69840(17) 0.8490(5) 0.0532 1.0000 Uani
C20 C -0.3702(5) 0.73844(15) 0.8463(4) 0.0409 1.0000 Uani
C21 C -0.2778(5) 0.75295(13) 0.7479(4) 0.0337 1.0000 Uani
C22 C 0.0261(4) 0.76704(11) 0.5951(3) 0.0250 1.0000 Uani
C23 C 0.1019(5) 0.75388(11) 0.7073(4) 0.0300 1.0000 Uani
C24 C 0.2477(5) 0.76976(13) 0.7476(4) 0.0363 1.0000 Uani
C25 C 0.3229(5) 0.79891(13) 0.6756(4) 0.0370 1.0000 Uani
C26 C 0.2500(5) 0.81227(12) 0.5658(4) 0.0354 1.0000 Uani
C27 C 0.1041(5) 0.79641(12) 0.5244(4) 0.0295 1.0000 Uani
C28 C -0.2340(5) 0.77090(11) 0.4604(3) 0.0274 1.0000 Uani
C29 C -0.2591(5) 0.81132(11) 0.4880(4) 0.0294 1.0000 Uani
C30 C -0.3671(5) 0.83348(13) 0.4168(4) 0.0408 1.0000 Uani
C31 C -0.4506(6) 0.81706(15) 0.3167(4) 0.0444 1.0000 Uani
C32 C -0.4271(6) 0.77717(15) 0.2875(4) 0.0426 1.0000 Uani
C33 C -0.3198(5) 0.75451(12) 0.3604(4) 0.0345 1.0000 Uani
N2 N 0.4040(3) 0.47196(9) -0.2955(3) 0.0233 1.0000 Uani
C34 C 0.2374(4) 0.48476(10) -0.2711(3) 0.0247 1.0000 Uani
C35 C 0.2434(5) 0.49847(12) -0.1318(3) 0.0319 1.0000 Uani
C36 C 0.4196(5) 0.50923(11) -0.1069(3) 0.0308 1.0000 Uani
C37 C 0.5115(4) 0.47892(10) -0.1860(3) 0.0250 1.0000 Uani
C38 C 0.4364(4) 0.44969(10) -0.3997(3) 0.0258 1.0000 Uani
O7 O 0.3286(3) 0.43994(8) -0.4731(3) 0.0344 1.0000 Uani
C39 C 0.6096(5) 0.43889(12) -0.4252(4) 0.0349 1.0000 Uani
C40 C 0.1832(4) 0.51619(10) -0.3688(3) 0.0245 1.0000 Uani
C41 C 0.0028(5) 0.52179(10) -0.3674(4) 0.0268 1.0000 Uani
O8 O -0.0879(3) 0.50504(9) -0.2956(3) 0.0345 1.0000 Uani
O9 O -0.0444(3) 0.54682(8) -0.4586(3) 0.0314 1.0000 Uani
C42 C -0.2175(5) 0.55488(14) -0.4663(5) 0.0413 1.0000 Uani
C43 C -0.2436(6) 0.58434(17) -0.5712(5) 0.0553 1.0000 Uani
C44 C 0.2738(4) 0.55551(10) -0.3543(4) 0.0271 1.0000 Uani
O10 O 0.4011(3) 0.56247(9) -0.3986(3) 0.0423 1.0000 Uani
O11 O 0.1923(3) 0.58018(8) -0.2774(3) 0.0307 1.0000 Uani
C45 C 0.2681(5) 0.61842(12) -0.2509(4) 0.0364 1.0000 Uani
C46 C 0.1410(6) 0.64537(13) -0.2002(5) 0.0472 1.0000 Uani
C47 C 0.5330(5) 0.43962(11) -0.1142(4) 0.0288 1.0000 Uani
O12 O 0.6451(3) 0.44595(7) -0.0136(2) 0.0267 1.0000 Uani
C48 C 0.6956(4) 0.41035(10) 0.0533(3) 0.0252 1.0000 Uani
C49 C 0.7982(4) 0.42543(11) 0.1654(3) 0.0248 1.0000 Uani
C50 C 0.8411(5) 0.46482(12) 0.1787(4) 0.0369 1.0000 Uani
C51 C 0.9319(6) 0.47674(14) 0.2848(5) 0.0470 1.0000 Uani
C52 C 0.9803(5) 0.44994(15) 0.3759(4) 0.0425 1.0000 Uani
C53 C 0.9368(5) 0.41027(14) 0.3631(4) 0.0370 1.0000 Uani
C54 C 0.8471(5) 0.39820(11) 0.2586(4) 0.0301 1.0000 Uani
C55 C 0.5433(4) 0.38912(10) 0.0993(3) 0.0250 1.0000 Uani
C56 C 0.4681(5) 0.40207(11) 0.2085(4) 0.0294 1.0000 Uani
C57 C 0.3180(5) 0.38756(13) 0.2442(4) 0.0360 1.0000 Uani
C58 C 0.2424(5) 0.35933(13) 0.1701(4) 0.0374 1.0000 Uani
C59 C 0.3162(5) 0.34560(12) 0.0611(4) 0.0370 1.0000 Uani
C60 C 0.4655(5) 0.36018(12) 0.0262(3) 0.0293 1.0000 Uani
C61 C 0.8036(5) 0.38530(11) -0.0330(3) 0.0267 1.0000 Uani
C62 C 0.8235(5) 0.34472(12) -0.0130(4) 0.0331 1.0000 Uani
C63 C 0.9262(6) 0.32273(13) -0.0907(4) 0.0419 1.0000 Uani
C64 C 1.0093(5) 0.34078(15) -0.1870(4) 0.0437 1.0000 Uani
C65 C 0.9928(5) 0.38106(14) -0.2067(4) 0.0402 1.0000 Uani
C66 C 0.8912(5) 0.40352(12) -0.1300(4) 0.0321 1.0000 Uani
H11 H 0.4250 0.6925 0.2150 0.0323 1.0000 Uiso
H21 H 0.3726 0.6808 0.4218 0.0408 1.0000 Uiso
H22 H 0.4057 0.6349 0.3794 0.0408 1.0000 Uiso
H31 H 0.1325 0.6522 0.4807 0.0381 1.0000 Uiso
H32 H 0.1347 0.6207 0.3628 0.0381 1.0000 Uiso
H41 H -0.0458 0.6682 0.2832 0.0326 1.0000 Uiso
H61 H -0.1057 0.7029 0.1323 0.0457 1.0000 Uiso
H62 H -0.0548 0.7420 0.0505 0.0457 1.0000 Uiso
H63 H -0.0694 0.6988 -0.0192 0.0457 1.0000 Uiso
H71 H 0.3610 0.6488 0.0427 0.0290 1.0000 Uiso
H91 H 0.8472 0.6235 0.0145 0.0515 1.0000 Uiso
H92 H 0.8268 0.5883 0.1198 0.0515 1.0000 Uiso
H101 H 0.9280 0.5618 -0.0716 0.0607 1.0000 Uiso
H102 H 0.7701 0.5787 -0.1480 0.0607 1.0000 Uiso
H103 H 0.7498 0.5435 -0.0427 0.0607 1.0000 Uiso
H121 H 0.2066 0.5422 0.3120 0.0427 1.0000 Uiso
H122 H 0.2494 0.5264 0.1697 0.0427 1.0000 Uiso
H131 H 0.3672 0.4842 0.3247 0.0529 1.0000 Uiso
H132 H 0.4642 0.5221 0.3850 0.0529 1.0000 Uiso
H133 H 0.5070 0.5063 0.2427 0.0529 1.0000 Uiso
H141 H 0.0000 0.7384 0.3161 0.0344 1.0000 Uiso
H142 H 0.1474 0.7269 0.4132 0.0344 1.0000 Uiso
H171 H -0.2317 0.6701 0.5868 0.0492 1.0000 Uiso
H181 H -0.3881 0.6454 0.7574 0.0694 1.0000 Uiso
H191 H -0.4769 0.6876 0.9197 0.0640 1.0000 Uiso
H201 H -0.4077 0.7567 0.9149 0.0492 1.0000 Uiso
H211 H -0.2496 0.7818 0.7456 0.0405 1.0000 Uiso
H231 H 0.0496 0.7327 0.7590 0.0361 1.0000 Uiso
H241 H 0.2990 0.7603 0.8285 0.0436 1.0000 Uiso
H251 H 0.4292 0.8101 0.7035 0.0444 1.0000 Uiso
H261 H 0.3026 0.8337 0.5151 0.0425 1.0000 Uiso
H271 H 0.0543 0.8061 0.4432 0.0355 1.0000 Uiso
H291 H -0.1982 0.8241 0.5596 0.0354 1.0000 Uiso
H301 H -0.3848 0.8620 0.4386 0.0490 1.0000 Uiso
H311 H -0.5274 0.8335 0.2653 0.0534 1.0000 Uiso
H321 H -0.4869 0.7648 0.2147 0.0510 1.0000 Uiso
H331 H -0.3047 0.7258 0.3396 0.0414 1.0000 Uiso
H341 H 0.1537 0.4636 -0.2820 0.0297 1.0000 Uiso
H351 H 0.1725 0.5221 -0.1193 0.0383 1.0000 Uiso
H352 H 0.2087 0.4766 -0.0741 0.0383 1.0000 Uiso
H361 H 0.4430 0.5369 -0.1356 0.0370 1.0000 Uiso
H362 H 0.4476 0.5066 -0.0147 0.0370 1.0000 Uiso
H371 H 0.6215 0.4886 -0.2083 0.0300 1.0000 Uiso
H391 H 0.6800 0.4493 -0.3552 0.0419 1.0000 Uiso
H392 H 0.6433 0.4508 -0.5077 0.0419 1.0000 Uiso
H393 H 0.6204 0.4093 -0.4297 0.0419 1.0000 Uiso
H401 H 0.2123 0.5058 -0.4544 0.0293 1.0000 Uiso
H421 H -0.2556 0.5662 -0.3841 0.0495 1.0000 Uiso
H422 H -0.2776 0.5298 -0.4854 0.0495 1.0000 Uiso
H431 H -0.3611 0.5906 -0.5792 0.0662 1.0000 Uiso
H432 H -0.1826 0.6092 -0.5516 0.0662 1.0000 Uiso
H433 H -0.2046 0.5729 -0.6529 0.0662 1.0000 Uiso
H451 H 0.3134 0.6298 -0.3307 0.0436 1.0000 Uiso
H452 H 0.3565 0.6151 -0.1865 0.0436 1.0000 Uiso
H461 H 0.1892 0.6719 -0.1810 0.0565 1.0000 Uiso
H462 H 0.0528 0.6484 -0.2650 0.0565 1.0000 Uiso
H463 H 0.0959 0.6337 -0.1208 0.0565 1.0000 Uiso
H471 H 0.5746 0.4188 -0.1730 0.0344 1.0000 Uiso
H472 H 0.4273 0.4309 -0.0790 0.0344 1.0000 Uiso
H501 H 0.8075 0.4847 0.1130 0.0442 1.0000 Uiso
H511 H 0.9622 0.5053 0.2945 0.0564 1.0000 Uiso
H521 H 1.0462 0.4589 0.4507 0.0510 1.0000 Uiso
H531 H 0.9702 0.3905 0.4292 0.0444 1.0000 Uiso
H541 H 0.8168 0.3696 0.2494 0.0361 1.0000 Uiso
H561 H 0.5230 0.4224 0.2631 0.0353 1.0000 Uiso
H571 H 0.2657 0.3976 0.3231 0.0433 1.0000 Uiso
H581 H 0.1346 0.3488 0.1948 0.0449 1.0000 Uiso
H591 H 0.2614 0.3251 0.0074 0.0443 1.0000 Uiso
H601 H 0.5181 0.3499 -0.0522 0.0351 1.0000 Uiso
H621 H 0.7642 0.3312 0.0570 0.0398 1.0000 Uiso
H631 H 0.9394 0.2936 -0.0759 0.0503 1.0000 Uiso
H641 H 1.0814 0.3248 -0.2426 0.0524 1.0000 Uiso
H651 H 1.0539 0.3943 -0.2763 0.0483 1.0000 Uiso
H661 H 0.8809 0.4328 -0.1443 0.0386 1.0000 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . N1 . C4 . 113.1(3) yes
C1 . N1 . C5 . 120.1(3) yes
C4 . N1 . C5 . 126.3(3) yes
N1 . C1 . C2 . 103.5(3) yes
N1 . C1 . C7 . 109.9(3) yes
C2 . C1 . C7 . 115.9(3) yes
N1 . C1 . H11 . 115.530 no
C2 . C1 . H11 . 109.525 no
C7 . C1 . H11 . 103.051 no
C1 . C2 . C3 . 104.8(3) yes
C1 . C2 . H21 . 110.627 no
C3 . C2 . H21 . 110.627 no
C1 . C2 . H22 . 110.627 no
C3 . C2 . H22 . 110.627 no
H21 . C2 . H22 . 109.466 no
C2 . C3 . C4 . 104.5(3) yes
C2 . C3 . H31 . 110.696 no
C4 . C3 . H31 . 110.696 no
C2 . C3 . H32 . 110.696 no
C4 . C3 . H32 . 110.696 no
H31 . C3 . H32 . 109.467 no
N1 . C4 . C3 . 102.5(3) yes
N1 . C4 . C14 . 108.4(3) yes
C3 . C4 . C14 . 110.9(3) yes
N1 . C4 . H41 . 115.057 no
C3 . C4 . H41 . 112.725 no
C14 . C4 . H41 . 107.183 no
N1 . C5 . O1 . 121.2(4) yes
N1 . C5 . C6 . 117.6(4) yes
O1 . C5 . C6 . 121.2(4) yes
C5 . C6 . H61 . 109.467 no
C5 . C6 . H62 . 109.467 no
H61 . C6 . H62 . 109.476 no
C5 . C6 . H63 . 109.467 no
H61 . C6 . H63 . 109.475 no
H62 . C6 . H63 . 109.476 no
C1 . C7 . C8 . 110.7(3) yes
C1 . C7 . C11 . 112.6(3) yes
C8 . C7 . C11 . 112.8(3) yes
C1 . C7 . H71 . 107.673 no
C8 . C7 . H71 . 107.422 no
C11 . C7 . H71 . 105.272 no
C7 . C8 . O2 . 125.3(3) yes
C7 . C8 . O3 . 109.9(3) yes
O2 . C8 . O3 . 124.8(3) yes
C8 . O3 . C9 . 115.2(3) yes
O3 . C9 . C10 . 107.5(4) yes
O3 . C9 . H91 . 109.953 no
C10 . C9 . H91 . 109.953 no
O3 . C9 . H92 . 109.953 no
C10 . C9 . H92 . 109.953 no
H91 . C9 . H92 . 109.467 no
C9 . C10 . H101 . 109.467 no
C9 . C10 . H102 . 109.466 no
H101 . C10 . H102 . 109.476 no
C9 . C10 . H103 . 109.467 no
H101 . C10 . H103 . 109.476 no
H102 . C10 . H103 . 109.476 no
C7 . C11 . O4 . 123.9(3) yes
C7 . C11 . O5 . 111.4(3) yes
O4 . C11 . O5 . 124.6(3) yes
C11 . O5 . C12 . 116.3(3) yes
O5 . C12 . C13 . 107.4(3) yes
O5 . C12 . H121 . 109.979 no
C13 . C12 . H121 . 109.979 no
O5 . C12 . H122 . 109.979 no
C13 . C12 . H122 . 109.979 no
H121 . C12 . H122 . 109.467 no
C12 . C13 . H131 . 109.466 no
C12 . C13 . H132 . 109.466 no
H131 . C13 . H132 . 109.476 no
C12 . C13 . H133 . 109.467 no
H131 . C13 . H133 . 109.476 no
H132 . C13 . H133 . 109.476 no
C4 . C14 . O6 . 106.4(3) yes
C4 . C14 . H141 . 110.227 no
O6 . C14 . H141 . 110.227 no
C4 . C14 . H142 . 110.227 no
O6 . C14 . H142 . 110.227 no
H141 . C14 . H142 . 109.467 no
C14 . O6 . C15 . 116.0(3) yes
O6 . C15 . C16 . 103.9(3) yes
O6 . C15 . C22 . 108.5(3) yes
C16 . C15 . C22 . 111.4(3) yes
O6 . C15 . C28 . 110.0(3) yes
C16 . C15 . C28 . 108.0(3) yes
C22 . C15 . C28 . 114.5(3) yes
C15 . C16 . C17 . 121.9(4) yes
C15 . C16 . C21 . 119.3(3) yes
C17 . C16 . C21 . 118.7(4) yes
C16 . C17 . C18 . 119.9(4) yes
C16 . C17 . H171 . 120.036 no
C18 . C17 . H171 . 120.036 no
C17 . C18 . C19 . 121.4(5) yes
C17 . C18 . H181 . 119.299 no
C19 . C18 . H181 . 119.299 no
C18 . C19 . C20 . 119.5(4) yes
C18 . C19 . H191 . 120.261 no
C20 . C19 . H191 . 120.261 no
C19 . C20 . C21 . 119.5(4) yes
C19 . C20 . H201 . 120.231 no
C21 . C20 . H201 . 120.231 no
C16 . C21 . C20 . 120.9(4) yes
C16 . C21 . H211 . 119.550 no
C20 . C21 . H211 . 119.550 no
C15 . C22 . C23 . 119.9(3) yes
C15 . C22 . C27 . 121.8(3) yes
C23 . C22 . C27 . 117.7(4) yes
C22 . C23 . C24 . 121.2(4) yes
C22 . C23 . H231 . 119.407 no
C24 . C23 . H231 . 119.407 no
C23 . C24 . C25 . 120.0(4) yes
C23 . C24 . H241 . 119.988 no
C25 . C24 . H241 . 119.988 no
C24 . C25 . C26 . 119.5(4) yes
C24 . C25 . H251 . 120.229 no
C26 . C25 . H251 . 120.229 no
C25 . C26 . C27 . 120.8(4) yes
C25 . C26 . H261 . 119.604 no
C27 . C26 . H261 . 119.604 no
C22 . C27 . C26 . 120.8(4) yes
C22 . C27 . H271 . 119.617 no
C26 . C27 . H271 . 119.617 no
C15 . C28 . C29 . 120.8(3) yes
C15 . C28 . C33 . 121.1(3) yes
C29 . C28 . C33 . 117.9(4) yes
C28 . C29 . C30 . 120.4(4) yes
C28 . C29 . H291 . 119.785 no
C30 . C29 . H291 . 119.785 no
C29 . C30 . C31 . 121.3(4) yes
C29 . C30 . H301 . 119.375 no
C31 . C30 . H301 . 119.375 no
C30 . C31 . C32 . 119.2(4) yes
C30 . C31 . H311 . 120.396 no
C32 . C31 . H311 . 120.396 no
C31 . C32 . C33 . 119.7(4) yes
C31 . C32 . H321 . 120.133 no
C33 . C32 . H321 . 120.133 no
C28 . C33 . C32 . 121.4(4) yes
C28 . C33 . H331 . 119.281 no
C32 . C33 . H331 . 119.281 no
C34 . N2 . C37 . 112.3(3) yes
C34 . N2 . C38 . 119.7(3) yes
C37 . N2 . C38 . 126.8(3) yes
N2 . C34 . C35 . 103.5(3) yes
N2 . C34 . C40 . 110.7(3) yes
C35 . C34 . C40 . 115.9(3) yes
N2 . C34 . H341 . 115.070 no
C35 . C34 . H341 . 109.756 no
C40 . C34 . H341 . 102.432 no
C34 . C35 . C36 . 104.8(3) yes
C34 . C35 . H351 . 110.619 no
C36 . C35 . H351 . 110.619 no
C34 . C35 . H352 . 110.619 no
C36 . C35 . H352 . 110.619 no
H351 . C35 . H352 . 109.466 no
C35 . C36 . C37 . 103.3(3) yes
C35 . C36 . H361 . 110.981 no
C37 . C36 . H361 . 110.981 no
C35 . C36 . H362 . 110.981 no
C37 . C36 . H362 . 110.980 no
H361 . C36 . H362 . 109.466 no
N2 . C37 . C36 . 103.4(3) yes
N2 . C37 . C47 . 108.4(3) yes
C36 . C37 . C47 . 111.3(3) yes
N2 . C37 . H371 . 114.621 no
C36 . C37 . H371 . 111.873 no
C47 . C37 . H371 . 107.212 no
N2 . C38 . O7 . 120.7(3) yes
N2 . C38 . C39 . 118.3(3) yes
O7 . C38 . C39 . 121.0(3) yes
C38 . C39 . H391 . 109.466 no
C38 . C39 . H392 . 109.467 no
H391 . C39 . H392 . 109.476 no
C38 . C39 . H393 . 109.467 no
H391 . C39 . H393 . 109.476 no
H392 . C39 . H393 . 109.476 no
C34 . C40 . C41 . 111.2(3) yes
C34 . C40 . C44 . 112.9(3) yes
C41 . C40 . C44 . 112.2(3) yes
C34 . C40 . H401 . 106.801 no
C41 . C40 . H401 . 107.560 no
C44 . C40 . H401 . 105.708 no
C40 . C41 . O8 . 124.8(3) yes
C40 . C41 . O9 . 110.8(3) yes
O8 . C41 . O9 . 124.3(3) yes
C41 . O9 . C42 . 115.9(3) yes
O9 . C42 . C43 . 107.3(4) yes
O9 . C42 . H421 . 110.012 no
C43 . C42 . H421 . 110.013 no
O9 . C42 . H422 . 110.012 no
C43 . C42 . H422 . 110.013 no
H421 . C42 . H422 . 109.466 no
C42 . C43 . H431 . 109.466 no
C42 . C43 . H432 . 109.466 no
H431 . C43 . H432 . 109.476 no
C42 . C43 . H433 . 109.467 no
H431 . C43 . H433 . 109.476 no
H432 . C43 . H433 . 109.476 no
C40 . C44 . O10 . 124.9(3) yes
C40 . C44 . O11 . 110.1(3) yes
O10 . C44 . O11 . 124.8(3) yes
C44 . O11 . C45 . 116.2(3) yes
O11 . C45 . C46 . 107.4(4) yes
O11 . C45 . H451 . 109.982 no
C46 . C45 . H451 . 109.982 no
O11 . C45 . H452 . 109.982 no
C46 . C45 . H452 . 109.982 no
H451 . C45 . H452 . 109.466 no
C45 . C46 . H461 . 109.467 no
C45 . C46 . H462 . 109.467 no
H461 . C46 . H462 . 109.475 no
C45 . C46 . H463 . 109.467 no
H461 . C46 . H463 . 109.476 no
H462 . C46 . H463 . 109.476 no
C37 . C47 . O12 . 108.1(3) yes
C37 . C47 . H471 . 109.821 no
O12 . C47 . H471 . 109.821 no
C37 . C47 . H472 . 109.821 no
O12 . C47 . H472 . 109.821 no
H471 . C47 . H472 . 109.467 no
C47 . O12 . C48 . 115.0(3) yes
O12 . C48 . C49 . 104.8(3) yes
O12 . C48 . C55 . 107.7(3) yes
C49 . C48 . C55 . 111.3(3) yes
O12 . C48 . C61 . 109.5(3) yes
C49 . C48 . C61 . 108.3(3) yes
C55 . C48 . C61 . 114.8(3) yes
C48 . C49 . C50 . 122.4(3) yes
C48 . C49 . C54 . 118.5(3) yes
C50 . C49 . C54 . 119.1(4) yes
C49 . C50 . C51 . 119.5(4) yes
C49 . C50 . H501 . 120.250 no
C51 . C50 . H501 . 120.250 no
C50 . C51 . C52 . 121.3(4) yes
C50 . C51 . H511 . 119.339 no
C52 . C51 . H511 . 119.339 no
C51 . C52 . C53 . 119.3(4) yes
C51 . C52 . H521 . 120.341 no
C53 . C52 . H521 . 120.342 no
C52 . C53 . C54 . 119.8(4) yes
C52 . C53 . H531 . 120.098 no
C54 . C53 . H531 . 120.099 no
C49 . C54 . C53 . 121.0(4) yes
C49 . C54 . H541 . 119.510 no
C53 . C54 . H541 . 119.511 no
C48 . C55 . C56 . 119.7(3) yes
C48 . C55 . C60 . 121.9(3) yes
C56 . C55 . C60 . 117.9(3) yes
C55 . C56 . C57 . 121.7(4) yes
C55 . C56 . H561 . 119.130 no
C57 . C56 . H561 . 119.130 no
C56 . C57 . C58 . 119.5(4) yes
C56 . C57 . H571 . 120.265 no
C58 . C57 . H571 . 120.265 no
C57 . C58 . C59 . 119.8(4) yes
C57 . C58 . H581 . 120.103 no
C59 . C58 . H581 . 120.102 no
C58 . C59 . C60 . 120.4(4) yes
C58 . C59 . H591 . 119.802 no
C60 . C59 . H591 . 119.802 no
C55 . C60 . C59 . 120.6(4) yes
C55 . C60 . H601 . 119.676 no
C59 . C60 . H601 . 119.676 no
C48 . C61 . C62 . 121.2(3) yes
C48 . C61 . C66 . 120.1(3) yes
C62 . C61 . C66 . 118.6(4) yes
C61 . C62 . C63 . 120.2(4) yes
C61 . C62 . H621 . 119.909 no
C63 . C62 . H621 . 119.909 no
C62 . C63 . C64 . 120.7(4) yes
C62 . C63 . H631 . 119.637 no
C64 . C63 . H631 . 119.637 no
C63 . C64 . C65 . 119.8(4) yes
C63 . C64 . H641 . 120.111 no
C65 . C64 . H641 . 120.111 no
C64 . C65 . C66 . 120.3(4) yes
C64 . C65 . H651 . 119.837 no
C66 . C65 . H651 . 119.837 no
C61 . C66 . C65 . 120.4(4) yes
C61 . C66 . H661 . 119.799 no
C65 . C66 . H661 . 119.799 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C1 . 1.481(5) yes
N1 . C4 . 1.473(5) yes
N1 . C5 . 1.357(5) yes
C1 . C2 . 1.529(5) yes
C1 . C7 . 1.550(5) yes
C1 . H11 . 1.000 no
C2 . C3 . 1.532(6) yes
C2 . H21 . 1.000 no
C2 . H22 . 1.000 no
C3 . C4 . 1.528(5) yes
C3 . H31 . 1.000 no
C3 . H32 . 1.000 no
C4 . C14 . 1.535(5) yes
C4 . H41 . 1.000 no
C5 . O1 . 1.231(5) yes
C5 . C6 . 1.513(6) yes
C6 . H61 . 1.000 no
C6 . H62 . 1.000 no
C6 . H63 . 1.000 no
C7 . C8 . 1.513(5) yes
C7 . C11 . 1.525(5) yes
C7 . H71 . 1.000 no
C8 . O2 . 1.194(5) yes
C8 . O3 . 1.347(4) yes
O3 . C9 . 1.462(5) yes
C9 . C10 . 1.495(7) yes
C9 . H91 . 1.000 no
C9 . H92 . 1.000 no
C10 . H101 . 1.000 no
C10 . H102 . 1.000 no
C10 . H103 . 1.000 no
C11 . O4 . 1.196(5) yes
C11 . O5 . 1.328(4) yes
O5 . C12 . 1.466(4) yes
C12 . C13 . 1.495(6) yes
C12 . H121 . 1.000 no
C12 . H122 . 1.000 no
C13 . H131 . 1.000 no
C13 . H132 . 1.000 no
C13 . H133 . 1.000 no
C14 . O6 . 1.418(4) yes
C14 . H141 . 1.000 no
C14 . H142 . 1.000 no
O6 . C15 . 1.450(4) yes
C15 . C16 . 1.542(5) yes
C15 . C22 . 1.526(5) yes
C15 . C28 . 1.533(5) yes
C16 . C17 . 1.378(6) yes
C16 . C21 . 1.388(6) yes
C17 . C18 . 1.389(6) yes
C17 . H171 . 1.000 no
C18 . C19 . 1.354(8) yes
C18 . H181 . 1.000 no
C19 . C20 . 1.390(8) yes
C19 . H191 . 1.000 no
C20 . C21 . 1.385(6) yes
C20 . H201 . 1.000 no
C21 . H211 . 1.000 no
C22 . C23 . 1.404(5) yes
C22 . C27 . 1.401(5) yes
C23 . C24 . 1.386(6) yes
C23 . H231 . 1.000 no
C24 . C25 . 1.392(6) yes
C24 . H241 . 1.000 no
C25 . C26 . 1.375(6) yes
C25 . H251 . 1.000 no
C26 . C27 . 1.389(6) yes
C26 . H261 . 1.000 no
C27 . H271 . 1.000 no
C28 . C29 . 1.408(5) yes
C28 . C33 . 1.380(6) yes
C29 . C30 . 1.382(6) yes
C29 . H291 . 1.000 no
C30 . C31 . 1.371(7) yes
C30 . H301 . 1.000 no
C31 . C32 . 1.392(7) yes
C31 . H311 . 1.000 no
C32 . C33 . 1.396(6) yes
C32 . H321 . 1.000 no
C33 . H331 . 1.000 no
N2 . C34 . 1.474(5) yes
N2 . C37 . 1.468(5) yes
N2 . C38 . 1.359(5) yes
C34 . C35 . 1.538(5) yes
C34 . C40 . 1.539(5) yes
C34 . H341 . 1.000 no
C35 . C36 . 1.527(6) yes
C35 . H351 . 1.000 no
C35 . H352 . 1.000 no
C36 . C37 . 1.527(5) yes
C36 . H361 . 1.000 no
C36 . H362 . 1.000 no
C37 . C47 . 1.534(5) yes
C37 . H371 . 1.000 no
C38 . O7 . 1.221(5) yes
C38 . C39 . 1.510(5) yes
C39 . H391 . 1.000 no
C39 . H392 . 1.000 no
C39 . H393 . 1.000 no
C40 . C41 . 1.509(5) yes
C40 . C44 . 1.529(5) yes
C40 . H401 . 1.000 no
C41 . O8 . 1.212(5) yes
C41 . O9 . 1.334(5) yes
O9 . C42 . 1.464(5) yes
C42 . C43 . 1.499(7) yes
C42 . H421 . 1.000 no
C42 . H422 . 1.000 no
C43 . H431 . 1.000 no
C43 . H432 . 1.000 no
C43 . H433 . 1.000 no
C44 . O10 . 1.183(5) yes
C44 . O11 . 1.347(4) yes
O11 . C45 . 1.459(5) yes
C45 . C46 . 1.495(6) yes
C45 . H451 . 1.000 no
C45 . H452 . 1.000 no
C46 . H461 . 1.000 no
C46 . H462 . 1.000 no
C46 . H463 . 1.000 no
C47 . O12 . 1.418(4) yes
C47 . H471 . 1.000 no
C47 . H472 . 1.000 no
O12 . C48 . 1.450(4) yes
C48 . C49 . 1.534(5) yes
C48 . C55 . 1.536(5) yes
C48 . C61 . 1.536(5) yes
C49 . C50 . 1.380(5) yes
C49 . C54 . 1.400(5) yes
C50 . C51 . 1.400(6) yes
C50 . H501 . 1.000 no
C51 . C52 . 1.374(7) yes
C51 . H511 . 1.000 no
C52 . C53 . 1.390(7) yes
C52 . H521 . 1.000 no
C53 . C54 . 1.383(6) yes
C53 . H531 . 1.000 no
C54 . H541 . 1.000 no
C55 . C56 . 1.384(5) yes
C55 . C60 . 1.396(5) yes
C56 . C57 . 1.394(6) yes
C56 . H561 . 1.000 no
C57 . C58 . 1.377(6) yes
C57 . H571 . 1.000 no
C58 . C59 . 1.386(6) yes
C58 . H581 . 1.000 no
C59 . C60 . 1.387(6) yes
C59 . H591 . 1.000 no
C60 . H601 . 1.000 no
C61 . C62 . 1.392(5) yes
C61 . C66 . 1.402(6) yes
C62 . C63 . 1.400(6) yes
C62 . H621 . 1.000 no
C63 . C64 . 1.374(7) yes
C63 . H631 . 1.000 no
C64 . C65 . 1.379(7) yes
C64 . H641 . 1.000 no
C65 . C66 . 1.397(6) yes
C65 . H651 . 1.000 no
C66 . H661 . 1.000 no
